Toluene → 36626-03-6

HRID 1593755Notes

Reaction equation

HRID 1593755 reaction equation
[NH2:1][CH:2]=[C:3]([C:7]#[N:8])[C:4]([NH2:6])=O.P(Cl)(Cl)(Cl)=O.[C:14]1(C)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C.C(#N)CCC.C1(C)C(C)=CC=CC=1>[NH2:6][C:4]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:1]=[CH:2][C:3]=1[C:7]#[N:8]

Participants

7

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 231663HCID 231663, compound

Product 1

HCID 1242840136626-03-6

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 7237O-XyleneSolventHCID 8008ButyronitrileSolvent

Procedure

The present invention relates to a process for the preparation of a 4-amino-3-quinolinecarbonitrile comprising combining an amine compound with cyanoacetic acid and an acid catalyst to yield a cyanoacetamide; condensing the cyanoacetamide with an optionally up to tetra-substituted aniline in an alcoholic solvent and a trialkylorthoformate to yield a 3-amino-2-cyanoacrylamide, and then combining the 3-amino-2-cyanoacrylamide with phosphorus oxychloride in acetonitrile, butyronitrile, toluene or xylene, optionally in the presence of a catalyst to yield a 4-amino-3-quinolinecarbonitrile.

Sources & evidence

ORD record
ord-67009b044b0743338c10ceb9424d567b
Source dataset
uspto-grants-2007_11
Patent number
US07297795B2

Reaction notes

Loading…